1 Mate: Beggin’ yer pardon, cap’n, but sailing from island to island west to east is against the prevailing winds.
2 Mate: It’ll take much longer than sailing to, say, Martinique, and then searching westwards for the pirates.
3 Ponsonby: The canny hunter always approaches his prey from downwind, Mister Mate!
4 Mate: So... we’ll smell them first?
4 Ponsonby: Exactly!
4 Mate: Eeeeurgh!!!

After the last time we saw Captain Ponsonby in #4219, the forums were full of comments about how sailing from Baracoa eastwards is against the prevailing winds in the Caribbean, making it a bad choice of direction. Followed by a some reasons why Ponsonby would deliberately choose to sail against the wind:

• Because he'd be expecting the pirates to be coming the other way, so this makes it easier to intercept them.
• Because he's being paid by the day, so he wants to take as long as possible.

However, in more practical terms, tactically you're far better off catching up to someone with the wind behind your back than running into them headlong with the wind behind them. The upwind ship has what is called the weather gage, giving it far greater manoeuvrability relative to the downwind ship. This was a critical consideration in ship-to-ship combat during the Age of Sail, and no doubt Ponsonby and the pirates would be intimately familiar with it.

So we can only assume that Ponsonby has some other good reason for sailing upwind. It means the pirates won't be able to smell them coming...